The Jacksonville Jaguars were the talk of the NFL Wednesday after they decided to relieve Tom Coughlin of his duties as the team’s front office leader. He had been with the team since 2017 and was brought in to help get the franchise on the right track. He was able to do that during his first year, however, his formula proved not to be a sustainable way to win.
Along the way, there were also crucial mistakes made that ultimately prevented success for the franchise. Here are the five most significant ones that Coughlin had his hand in:

5. Not keeping WR Allen Robinson
One of the unfortunate trends fans witnessed during Coughlin’s run was him letting good players go. The first of those players was receiver Allen Robinson, who is still finding a way to be successful despite the struggles of Mitch Trubisky over with the Chicago Bears.
In an interview from February with ESPN 690AM, Robinson revealed that he and the Jags were“decently close” to a contract extension before the 2017 season, and in looking back at things in hindsight, life could’ve been better for Coughlin if the Jags would’ve just sweetened the pot. Sure, they presently have a stud in D.J. Chark, but most fans tend to agree the Jags need a No. 2 beside him as Dede Westbrook and Chris Conley haven’t wowed anyone this year.
Now, the Jags will enter the offseason with the need for an explosive playmaker next to Chark when the fact of the matter is that it’s possible he could’ve been paired with Robinson for years to come.
Could you guys imagine that duo? I certainly could.

4. Free-agent spending habits
The issue that Coughlin had in his first stint with the Jags was his management with the salary cap and his habits in free-agency, which ultimately turned out to be his undoing. In his second stint with the team, it appears as though he simply didn’t learn from those mistakes.
With Coughlin returning as an executive, the Jags consistently picked up high priced free-agents as if they were close to being competitive. As the good franchises in the league have shown, that’s not a way to build a team.
Additionally, some of the free-agent acquisitions made haven’t been wise investments. Andrew Norwell was made the league’s highest-paid guard when he signed and hasn’t been all that impressive since.
Of course, there is also the contract the Jags handed out to veteran quarterback Nick Foles, which is the biggest free-agent contract in team history but looks to be another miss. Both are earning money that could’ve been handed to players who have performed well like defensive end Yannick Ngakoue or perhaps Jalen Ramsey, which brings me to my next point…

3. The Jalen Ramsey saga
I’m on record for saying Jalen Ramsey didn’t handle his saga with the Jags well, but neither did they. As an organization in the league, it’s never good when you can’t find common ground with your franchise player and don’t so much as shoot him one contract offer. The players on the outside looking in will definitely develop their perceptions of the organization, most of which might not be good.
It’s well documented that Coughlin had his share of run-ins with Ramsey. With him having such a strong personality, the two never saw eye-to-eye and it led to Ramsey leaving although I believe that wasn’t his only reason for departing. However, it’s a possibility that Ramsey could’ve remained with the team if they offered him the right kind of extension, but fans will never know.
In an era where players like to feel appreciated, pending free-agents and players currently on the roster are likely confused about what it takes to be rewarded by this franchise. It also doesn’t help for them to witness the Jags prioritize outsiders (free-agents) over homegrown talent (players drafted by the Jags) who’ve put together a solid body of work on the field.

2. Run-ins with the NFLPA
Speaking of the league’s perception of the Jags, the NFLPA’s statements on Monday weren’t a good look at all. The union singled out the organization and it has made them look like the worst franchise in the NFL. As a result, Khan took action (albeit late) and he fired Coughlin, who was going to retire at the end of the season.
The first grievance the Jags were hit with this week was filed by Dante Fowler Jr., who was wrongfully fined for not rehabbing at the Jags’ facility during the 2018 offseason. The other grievance came from Leonard Fournette, who the Jags fined for being inactive with an ankle injury in 2018’s season finale against the Houston Texans. Thankfully, both players were able to recoup their money
While Coughlin may be out of the picture, the perception on the Jags likely won’t change anytime soon and that’s something Khan is going to have to fix. It also probably won’t benefit Coughlin’s reputation though his résumé as a coach is pretty solid in terms of production.

1. Poor decisions at QB
While heat from the NFLPA is what ultimately led to Khan firing Coughlin, his decisions at the quarterback position are the biggest factors that held the team back. When he returned as an executive for the Jags, many were quick to praise his evaluation skills on the offensive side of the football, however, he could never figure out the most important position in the game during his second run in Duval.
His first mistake involving the quarterback position was taking in Dave Caldwell’s project, Blake Bortles, and not his own. It’s hard to say if he simply wanted to avoid friction in the front office or let Caldwell persuade him to stick with Bortles longer than they should’ve, but Coughlin should’ve done what a lot of executives do early in their tenures: draft his own quarterback early. Instead, the team is still paying for that mistake financially while Bortles isn’t even on the team.
In the process of keeping Bortles, he passed on Deshaun Watson, Patrick Mahomes and Lamar Jackson, all MVP caliber players who could’ve elevated the Jags to new heights with the right offensive coordinator. Instead, he’ll now have to watch all or most of those quarterbacks lead their respective teams to the playoffs from home.
To make matters worse, Coughlin tried to patch up that mistake with Foles, who he made the highest-paid free-agent acquisition in team history. As we’re seeing now, that proved to not only hurt the Jags’ cap situation like Bortles’ contract did, but it appears the veteran is also not the answer. To put it simply, history has proven that free-agency isn’t where organizations find starting quarterbacks, and a veteran in the game like Coughlin definitely should’ve steered away from making such an avoidable mistake.